one that made it happen best for me.
“Curiously, she didn’t say anything about the asshole. I guess that wasn’t very sensitive for her. But I found out about it myself, once I really got into it and started doing it good. The first time I ever did it to myself was in the john at a little house we had. This was about six months before I left for the States and the boarding school, and it was absolutely the greatest, most exciting, most fulfilling discovery I’ve ever made in my entire life! “I’d already started having periods by that time, of course, and I’d developed a fairly thick growth of pussy fur and the lips of my pussy had already grown out pretty well. I don’t guess I ever had a cherry. The first time I ever put my finger in my cunt I rammed it in up to the palm and I never felt anything remotely resembling a cherry. I’ve heard that most girls don’t have them.
They’re’ mostly a figment of the guys’ imaginations, I guess.
“Anyway, I was sitting there on the john and finger fucking to beat the band this particular day. I was in the john because that was the safest place to be.
Since there was only the one bedroom in the cabin, I couldn’t do it in bed or else Mom and Dad would hear me when I started to come. I wasn’t having a whole lot of luck that afternoon and it seemed like the come was locked up some place way deep in my cunt. Nothing I could do would get it out. Finally I stopped gouging and just sat there, letting my fingers wander around all over the lips of my pussy.
“I’d already found out that that little patch of meat just to the rear of my cunt was pretty lively-you know, that spot between the cunt and the asshole. I was rubbing that, along with my clit, sort of working back and forth between them, and all of a sudden I asked myself, ‘Why not?” I mean, why not try sticking my finger in my, ass? As soon as the thought hit me I was gone. There wasn’t a thing in the world 1 could do about it! Man; it was positively the most exciting idea I’d ever had and I didn’t waste any time in getting to it.
“My fingers were already plenty slippery, from having been in my cunt. Even though I couldn’t come, I’d gotten myself hot enough that I was plenty wet and juicy. That finger slipped in just as easy as pie! And oh my, what a nice feeling! It was at least as sensitive as my cunt and when I thought of what Mom ‘would say if she could see me sitting there and finger fucking my own asshole, I just curled up inside. Well, I just drove the finger in good and deep and kept it there while I rubbed another finger over my clit. I couldn’t bear to move my finger around inside my ass very much, it hurt so much, but by just leaving it there and keeping it still I managed to get myself a really first-class come out, of it.
“As soon as the come hit me, I knew that I’d stumbled onto something really big. I didn’t dare even think about it much, it affected me so, but I just knew deep down inside that I’d graduated into the real big leagues. From the way Mom had always talked, I knew that it was wrong to play with your asshole and that it was a very nasty part of your body but hell, there were times when I just couldn’t keep from doing it to myself. It always really knocked me for a loop, fingering myself in the butt, but there were times when I just seemed to be all knotted up inside and there wasn’t any way I could keep from doing it to myself that way. I don’t know quite what it was that made me do it, or why. I could come so much more strongly with my finger in my ass.
“It sure wasn’t just because of the extra pleasure! Why, there were times when I felt so bad about doing it that way that I thought about running away or maybe even trying suicide or something like that. Why, there were times I could almost cry, I felt so bad about the things I did to myself! I just knew that I was turning into a queer; or some kind of pervert, but in spite of all that, I’d still win4 up sitting in the john about once a month and gouging hell out of my fanny.
“Starting to date when I was in boarding school didn’t help either. It was a pretty classy school, I guess, and just about all the girls were really into sex. My roommate, Lois, was one of the worst ‘of the lot. She was from a really rich New York family and she had just about every kind of hang-up there is. She used to tell me that she hated to tuck, but that even more she hated not doing it. So she usually wound up with a prick up her cunt. I don’t know what her problem was but she used to do her studying with a book in one hand and her pussy’ in the other! “Well, Lois found, out that I sometimes finger fucked myself in the ass. I couldn’t keep it from her. It just came out one day when we were talking about what we’d done in the sex line. She wanted to know if I’d ever let a guy tuck me there. Wow! I’d barely even let guys get their ‘cocks up my cunt, I was that green, but I had let a couple of guys screw me. It hadn’t done amp; whole lot for me,” partly because… well, I guess I was just too used to doing it my own way.
“The more I thought about what Lois had’ said, the more, hung up I became. I mean, there was part of me that was saying ‘Do it!” and then there was another part of me that was saying ‘Don’t!” So I was pulled in both directions at once.
I wanted to and I didn’t. I knew that it was terribly wrong and that ‘people shouldn’t do it that way but, at the same time, I really wanted to take a fellow that way. I just couldn’t get the thought out of my mind-the idea of a medium-sized cock sliding into my ass, filling me full of hard meat an4 then shooting come in way deep. That really turned me on. There were times when I’d turn into jelly it seemed, just by letting thoughts like that run through my mind.
“I’ll always believe that Lois clued that guy in, the first time I ever got tucked in the asshole. See, she and I’d gone up to this college for a weekend date with- a couple of guys that she knew pretty well. She was already thick with both of them and she told me all about Ricky, the guy I was supposed to be dating for the weekend…
“He doesn’t have a really big prick,” she’ told me, ‘but that thing is just made of solid steel! He can pump all night if he wants to and never let a drop of come out. You’ll really have a ball with him. And he just loves eating a girl’s cunt out!”
“With a recommendation like that, you can bet that I was looking forward to the weekend with mixed emotions. Lois made it crystal clear that she was going only because of Tim, the other guy. He had a cock the size of a post, it seemed, and she was always red hot to take on the biggest guy around.’ Neither one of us said anything about doing it in the ass, but I still think she’d already told Ricky to try me out that way. I was mostly wondering what it would be like to have a guy eating my pussy. I hadn’t ever had a fellow do that to me before.
“The weekend was about like any of twenty or thirty others that I went on while I was in boarding school-a football game, a dance, a couple of parties. And a lot of sex mixed in between all that other stuff. It was a pretty busy time.
The first chance Ricky and I got, we slipped off and started making out. Just like Lois said, he was really hot to go down on me and I… well, I thought it was pretty good. Especially when he started licking my asshole! Yeah, he was rubbing his tongue over the opening and trying to stick it in me! “That really knocked me out and when he switched around I just couldn’t say no to him. I laid there and watched while he ran his cock into my cunt to get it slippery and then well, he just shot that cock right up my asshole! I guess all the practice I’d already had, doing myself with my finger, was enough to loosen me up for him. Anyway, I didn’t have any trouble at all in getting him inside me.
“I reached down to make sure that he really was going into my ass and there wasn’t a bit of doubt about it. His cock was right in the middle of my ass! I was already about half silly it felt ‘so damned — good, and then I started fingering my ditty and cunt while he was fucking my ass pretty hard. God, it was just out of sight, all that feeling mixed in together and with me thinking all the time, I’ve done it now I’ve got a guy in my ass! I was lying on my back with my legs up in the air, so I couldn’t move too much, but I could squeeze my asshole-you just bear down, as if you were trying to shit- and that made it real good for Ricky.
“Great tucking!” he told me. “You’ve got the greatest asshole in the world!”
“Fuck it then,” I told him. “Fuck my ass- hole! Fuck-the shit out of me!”
“He did it. Man, I was just coming all over and when I felt him let go with his come it was simply incredible, the way my clit and cunt and asshole all started working together and making it better than ever!”
Judy C. the source of the case history considered ‘in this Chapter, came to our attention through the ‘alertness of a colleague conducting sensitivity training sessions for business executives and certain selected employees of the firms employing those executives. Judy was personal secretary to the advertising director of a very large company. During the training session, which her employer did not attend, Judy admitted that she was- having an affair with her boss and they frequently resorted to anal intercourse. Certain other statements which she made during the training session caused the director to refer her to us. She subsequently agreed to cooperate with our research.
Judy’s fascination with anal sex can be understood by referring back to her earlier years. The reader may already have noticed how often her early sexual experiences were associated in some way with bathrooms or with
